


Put Your Diamonds Where Your Mouth Is

by AaronAmpora



Category: Hermitcraft RPF, Minecraft (Video Game)
Genre: Alcohol, Anal, Anal Fingering, Anal Sex, And no one is straight, Blow Jobs, Crossdressing, Cuddling & Snuggling, Daddy Kink, Dancing, Dom/sub, Drinking, Drunk Sex, Embarrassment, Explicit Consent, First Time Bottoming, Forced Crossdressing, Grian is a Tease, Hangover, Humiliation, Kissing, M/M, Muscles, Open Relationships, Party, Party Games, Polyamory, Praise Kink, Pretty much everyone is poly, Rough Kissing, Sexy Dancing, Stress is an Exhibitionist, Truth or Dare, season 6, soft dom
Language: English
Status: Completed
Published: 2020-03-12
Updated: 2020-03-12
Packaged: 2021-02-28 18:55:23
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,406
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23122102
Author URL: https://archiveofourown.org/users/AaronAmpora/pseuds/AaronAmpora
Summary: Iskall lost a bet, so now he has to wear the Dorothy skin for a week, including during the monthly hermit party. After a few too many drinks, Iskall bets that he can top Cub, and Cub takes him up on it. Things definitely don't go the way Iskall had planned, but he doesn't really mind in the end.
Relationships: Cub/Iskall, Cubfan135/Iskall85, Iskall/Mumbo/Grian, Iskall85/Mumbo Jumbo/Grian, Minor or Background Relationship(s)
Comments: 19
Kudos: 202





	Put Your Diamonds Where Your Mouth Is

**Author's Note:**

> Disclaimer: All characters depicted in this story are fictional personas, not real people. Please do not ship real people, it’s weird.  
> (also, to any hermits who might find this: I’m so fucking sorry)

Iskall gave a small groan that morphed into an incredulous laugh as he looked at himself in the mirror.

He looked like a fool.

His normally short, brunette hair was now much longer and pulled into two low pigtails that sat on his shoulders and were tied off with baby blue ribbons. While his body was covered in a white blouse with short, puffy sleeves, and a blue checked dress that came to his knees, then to finish it all off, he wore a pair of bright red, sparkly shoes with a 2 inch heel. Yup. He was Dorothy again.

The reason for his change in appearance was not to entice a sale from Scar, no, this time, it was because he had lost a bet to Mr. Goodtimes, and now had to wear the ensemble for a week.

Awesome.

Even worse was the fact that the monthly hermit party night was that night, so he’d be attending in full dress, if he went, which he was entertaining the idea of skipping this month, just because of the dress. But he quickly brushed the idea aside, if he didn’t show up, Scar would know why, he had to show that he wasn’t ashamed of wearing the flowy, fluttery, flashy outfit, even if it was a bit embarrassing. Especially anytime a breeze hit and lifted the skirt, even just a bit, since he was only wearing boxers under the dress and he didn’t exactly want to flash anyone.

His communicator suddenly beeped and he pulled it out, noticing he had a new message from Grian.

<Grian> hey Iskall, you coming tonight?  
<Iskall85> yeah of course. why do you ask?  
<Grian> well, I heard from a certain someone about your... ehem, costume change  
<Iskall85> hey man, I can rock this dress  
<Iskall85> it brings out my eyes  
<Grian> lol ok  
<Grian> see you tonight  
<Iskall85> yup, see you tonight

Iskall took a deep breath as he closed his communicator, then slowly let it out in a deep groan as he flopped onto his bed. Guess he’s got no choice now. He’s going to the party, in full Dorothy getup.

-

Iskall took a deep breath, steadying himself and putting on a confident smile as he walked toward the building. He could already hear the music and see lights flashing through the windows. He pushed open the door and entered, the music blasting from a DJ setup near the back of the room, where he could just barely make out Impulse working the table. Most everyone was already there, he could see Cleo, Stress, Zedaph, Tango, Grian, Scar, Jevin, and Ren all on the dance floor, all of them rocking out to the music. He looked around and saw Xisuma and Cub sitting on one of the couches in the lounge area off to the side, while Doc sat on another couch with BDubs and Keralis. Finally, he looked over at the bar they had set up on the wall closest to him, and saw Mumbo and False sitting on stools, and Joe behind the bar, whipping up a drink.

Mumbo spotted him and raised his drink, smiling and motioning Iskall towards him. He walked over and took the stool next to Mumbo, grinning.

“Hey Mumbo.”

“Hey Iskall, you want something to drink? Joe is quite talented at making mixed drinks, mine is fantastic and doesn’t even taste like alcohol!”

“Sure. Hey Joe, can you make me something strong and not too sweet?”

The brunette behind the bar nodded with a smile and set about making something. Iskall wasn’t even sure what most of the liquids he was adding were, but he trusted Joe so he just shrugged and turned to the dancefloor. He still felt a bit awkward in the dress, but he made sure not to show it, relaxing against the bar as his eyes scanned the area. Stress immediately caught his attention, she was seriously busting some moves and Iskall found he couldn’t look away. She stood back to back with Cleo, facing the bar, and swayed her hips in time with the music, her arms in the air and a happy smile on her face. She suddenly locked eyes with Iskall and a devious smirk appeared on her face. Without breaking eye-contact, she brought her hands down, starting around her breasts and running them along her curves, Iskall’s eyes followed her hands and he swallowed hard. Damn Stress had a nice body, curves in all the best places. She brought her hands back up and his eyes snapped back to her face, seeing the smirk still there, but now she was biting her bottom lip, nearly giving him bedroom eyes. He watched as Cleo turned around and saw what was going on, a grin forming on her lips as she grabbed Stress’s hips and started to grind against her ass in time to the music. Stress happily tangled her fingers in Cleo’s bright orange hair and ground back, the two practically dry-humping on the dance floor, though, that wasn’t exactly anything new.

Iskall’s attention snapped back to the people at the bar when he saw False get up and practically stalk over to the other two girls, pulling Stress into a deep kiss which had a few of the other hermits whooping and whistling. Iskall joined, grinning and laughing a bit before turning back to the bar, and seeing his drink sitting there. He grabbed it and took a swig.

“Holy crap that’s good.” He remarked, a bit in awe. He saw Joe grin at the praise before getting to work on another drink. Iskall turned to Mumbo and saw the mustached man was transfixed, his eyes stuck on the now three women dry humping on the dancefloor. Iskall chuckled and nudged Mumbo’s arm, grabbing the man’s attention. Mumbo looked startled for a moment, then embarrassed, the flush that had already started on his cheeks brightening, which caused Iskall to laugh and pat his friend on the back. Mumbo just groaned a bit, then laughed too.

“They are the worst.” The black-haired man groaned.

“Oh absolutely. But hey, at least they let us watch!” Iskall laughed a bit more, then took another sip of his drink. It was well known on the server that Cleo, False and Stress were in a poly triad and that they very rarely let anyone else join in. It was also well known, that Stress was a total exhibitionist and the other two indulged her, so it wasn’t unusual for them to engage in some pretty intense PDA.

Iskall took another sip, while trying not to stare at the trio but instead looking at all the other hermits on the dance floor. Apparently Keralis and BDubs had gotten bored just sitting off to the side, since they were now dancing with each other, their arms wrapped around the other’s body and their hips swaying together in time to the beat. Zedaph and Tango were dancing together, and it seemed to be some sort of actual dance, though Iskall had no idea what kind, but it involved Tango spinning Zed around and pulling him close before releasing him again. The two were laughing, and it was honestly kind of cute. He moved on and saw Grian was sandwiched between Scar and Ren, a shit-eating grin on his face as he ground his ass against Scar while leaning his chest against Ren’s. The two taller hermits were clearly enjoying it, but knowing Grian, he was going to leave them hanging pretty soon. He tended to be a little shit like that. Iskall knew from experience, having been in a similar position to Ren and Scar multiple times, though he generally would pull Grian into one of the back rooms for a quickie if the blonde got him too riled up. He chuckled a bit and leaned towards Mumbo.

“Get a look at Grian.” Iskall said and Mumbo followed the brunette’s gaze, laughing lightly when he saw what the prankster was up to.

“I feel a bit bad for them really. He’s such a tease.” The mustached man commented.

“Yeah, but hey, maybe Ren will finally get fed up and do what I usually do.” Iskall smirked a bit as he said it, and Mumbo blushed. He knew exactly what Iskall meant. Mumbo himself had been teased by Grian on many different occasions, but the suit-wearing hermit generally just got embarrassed and would extract himself from the area. He found getting some fresh air usually helped to calm him down. Now, it’s not like he’s a prude or anything, he’d had sex quite a few times and greatly enjoyed it, but he just didn’t have the gall to yank Grian off into a corner like Iskall did.

Iskall chuckled and took another sip of his drink, realizing with a bit of surprise that he had nearly finished it. He felt a bit buzzed, but not too much, so he turned around, asking Joe for another one. The bespectacled hermit nodded and got to work, and Iskall spun back around, looking back at the dancefloor to find that the female trio had moved over to the couches and were now in a full-on make-out session. Iskall finished his first drink just as the second one was slid towards him. He thanked Joe and pretty much downed the second drink before hopping off his bar stool and tugging Mumbo off of his. The taller hermit protested that he hadn’t finished his drink, so Iskall relented for a moment.

“Hurry up then!” He urged, and Mumbo chugged the last bit of his drink, just barely managing to set the glass down before he was unceremoniously dragged from his chair and onto the dancefloor.

-

After a few hours of dancing and drinking, the hermits were all tired and pleasantly drunk, some more so than others. They turned down the music and moved to the more relaxed part of the night, anyone who was still there, which was most of them, sat in a circle in the lounge area. The hermits remaining were, Iskall, of course, Mumbo, Grian, Tango, Zedaph, Impulse, False, Cleo, Stress, BDubs, Keralis, Doc, Scar, and Cub, though Cub wasn’t sitting with them, he was over at the bar, making drinks, since Joe had gone home for the night.

Iskall was quite drunk at this point, not so much that he couldn’t walk, but he was feeling good, and definitely stumbled a bit when he sat down, kind of falling more than sitting. He situated his skirt so the top was pinned under his thighs, and there was no gap for anyone to look up. He’d learned that technique from Stress the first time he’d worn the outfit. He settled in and slouched a bit, getting comfy and letting out a chuckle when Grian practically crawled onto the couch next to him, curling up against his side and cuddling close. Grian was always a touchy-feely sort of person, but it got increased tenfold when he was drunk. Mumbo on the other hand, sat on Iskall’s other side, just close enough that their thighs touched and Iskall could easily reach out and loop an arm around the tall man’s tiny waist. Which he did, as well as laying his other arm over Grian’s back.  
Once everyone was settled, they spent a while chatting, cracking jokes and making passes at each other, until Cleo burst through.

“Alright everyone! What are we playing tonight? Truth or Dare?”

“7 minutes in heaven!” Stress called out.

“Spin the bottle.” False suggested.

Iskall laughed a bit at the rather juvenile games they were suggesting, and felt Mumbo shift uncomfortably beside him.

“What are we, 14?” Mumbo asked, a bit incredulously.

“Oh come on Mumbo, it’ll be fun!” Stress laughed, her cheeks flushed, showing she was obviously quite drunk.

“I highly doubt that.” Mumbo mumbled, just as Tango spoke up.

“Personally, I vote Truth or Dare.” Zedaph nodded at the suggestion and most of the other hermits just shrugged.

“Truth or Dare it is!” Cleo announced. “Alright then, who wants to go first?” When no one immediately volunteered, Cleo spoke again. “I guess it’s me then. Impulse! Truth or Dare?”  
Impulse looked a bit surprised at being chosen, but took it in stride, laughing a bit as he answered.

“Truth.” Cleo looked a bit disappointed at his answer, obviously she had wanted him to pick dare. She was silent for a moment, then grinned.

“Is it true that you once fucked Tango in the middle of the battle field, during the Civil War?” Impulse’s eyes widened slightly and a blush rose to his face, and Tango started laughing.

“Uh, yeah… That’s true.” Impulse confessed and the rest of the group laughed, giving a few wolf-whistles and suggestive eyebrows directed towards the two. After a few moments, Impulse spoke again, clearing his throat a bit as he tried to get his blush to go down.

“Um, BDubs, Truth or Dare?” BDubs looked up from his spot, curled up against Keralis and smirked.

“Dare.”

“I dare you to…” He took a moment to think, but nothing interesting came to mind. “Kiss Keralis.” His dare got a few groans, mostly from the trio of ladies, but BDubs just smirked wider and shifted a bit so he could reach up and get a soft kiss from Keralis. He then turned back to the group.

“False, Truth or Dare?” He asked. The blonde smiled a bit.

“Dare, of course.” BDubs chuckled a bit at her answer.

“Hm… Then I dare you to…” He glanced over at the bar and smirked. “Drink a full shot of grenadine.” False recoiled, laughing.

“Ugh, that’s disgusting BDubs!” The black-haired hermit cackled.

“Do it!” He laughed. The blonde reluctantly stood, making a bit of a show of not wanting to as he walked over to the bar, where Cub had already poured her a shot of the bright red syrup. False made a face as she picked up the shot glass, turning to face the group before she tossed it back with a grimace. Gagging a bit as she finished and slammed the shot glass back on the bar.

“That was awful!” She shivered a bit and made her way back to cheers and laughter from her friends, plopping back into her spot. “Alright, Doc, Truth or Dare?”

“Truth.” The cyborg smirked, but the smirk fell a bit when False asked her question.

“Tell us your top 5 kinks.” False leaned back on the couch and the group watched Doc as he groaned, then wracked his brain.

“Uh, alright. In no particular order… Biting, bondage, knife play, inexperience, and uh, being called daddy.” The last one got a few whoops from the other hermits and he groaned. “Yeah, yeah…”

“Huh… Honestly, I’m kinda surprised. I would have figured you’d be more into being called master or something like that.” Grian piped up, making Doc flush slightly.

“Well, I mean, that too.” He admitted.

“Hah! Well, I think we all know who the main daddy of the server is.” BDubs chuckled, then paused when he got blank stares. “Uh, Cub, obviously! He’s the one that actually looks old enough to be any of our dads!” The other hermits laughed at that, everyone looking over at Cub, still behind the bar, who was just smirking at the conversation.

“I mean, you’re not wrong.” He chuckled and shrugged.

“Ooh daddy Cub!” Tango moaned in a high, falsetto voice, causing the whole group to burst into laughter, Cub included.

The conversation continued to derail for a bit and Iskall found himself losing interest, his mind focused more on the warmth of Grian and Mumbo beside him, giving Mumbo a light squeeze and gently rubbing Grian’s back. He was definitely drunk, his head spinning a bit as he stared at the ceiling. After what only seemed like a few moments, but was apparently longer, since it was now Stress’s turn, Iskall’s attention was snapped back by the small, brunette.

“Iskall! I said Truth or Dare?” Iskall groaned inwardly, but after the questions he had heard so far tonight, he knew his choice.

“I guess, dare.” Iskall realized his mistake when Stress’s eyes lit up and her grin widened.

“I dare you to call Cub Daddy for the rest of the night.” She giggled. Iskall’s jaw dropped and he felt blood rush to his face as the rest of the hermits started laughing, some of them, mostly Tango, nearly rolled off the couch they were laughing so hard. Of course, right at that moment, Cub came over to join the group, giving Iskall a smug smirk that had the brunette burning inside. Why did it have to be Cub!? The guy was already insufferable. Iskall just glared back and vowed he just wouldn’t talk to Cub for the rest of the night. He let out a small sigh, then realized he now had to pick someone.

“Hey, Zed, Truth or-” He was cut off by Cleo.

“Oh come on Iskall, that’s not fair, Zedaph’s already gone, but Cub hasn’t had a turn yet. You gotta ask him.” Her face was split in a shit-eating grin, and Iskall groaned, looking around to the other hermits for help, but they were all grinning and some were snickering at his misfortune. The brunette sighed, gritting his teeth.

“Fine. Daddy, Truth or Dare?” He couldn’t look at Cub as he said it, his face flushing brightly, but he got the words out, the group giggling and snickering as he did so.

“Hm… Let’s go with truth.” He could practically feel the smug rolling off of every word Cub said, and he growled a bit, glaring at nothing because he couldn’t bring himself to look at the older man.

“What is the most embarrassing moment of your life?” He said, trying not to growl. He suddenly noticed how stiff Mumbo and Grian were beside him, and that Grian was rubbing a hand gently over his chest, realizing his arms had gone stiff and tense around them, he consciously relaxed his muscles, and felt the other two relax as well. This bit of distraction caused him to miss what Cub said, but he really didn’t care, he just focused on keeping his arms relaxed, despite the fact that all he wanted to do was get up and punch Cub in his smug face. Or run from the room, either one would do.

The game continued and Iskall tried his best to stay out of it, not wanting to risk having to talk to Cub again, especially when the bastard kept shooting him glances, that smug smirk still planted in his lips. Unfortunately, his staying out of the game didn’t last much longer, but he didn’t realize it at first, since he wasn’t paying attention. But what did grab his attention was Cub waving at him and loudly speaking.

“Hey Princess, Scar asked you a question.” Iskall froze, then snapped his head up to glare directly at Cub, his cheeks bright red.

“The hell did you just call me?” He growled, but Cub just kept smirking.

“Princess. I mean, with that dress and the fact that you keep calling me daddy, it seems like a fitting title.” Iskall felt his whole face flush with embarrassment, he had almost forgotten about the dress. Cub chuckled at his blush. “Oh boy, Princess, I didn’t realize that putting you in a dress made you such a blushy bottom.” Iskall felt his blood boil and nearly jumped to his feet, though the room spun a bit when he did so and he stumbled, so it kind of ruined the aggression of the movement.

“Fuck you man! I can still top better than you, even in a dress!” Iskall slurred, and Cub just chuckled.

“Prove it then, Princess.” Cub stood from his spot next to Scar and Iskall felt his face get even hotter, but like hell he was going to back down now.

“Fine!” The brunette stomped over to Cub, grabbed the front of his lab coat and rather ungracefully smashed their mouths together. The older hermit wrapped one hand around Iskall’s waist and threaded the other through his abnormally long hair. Their lip-lock earned a few whoops and cheers from the other hermits, who were all watching this in shock. Finally they broke apart and Tango called.

“Get a room you two!” Which made Cub chuckle.

“Don’t mind if we do.” Cub used his grip around Iskall’s waist to steer the brunette away from the group and down the hall, wolf-whistles and cheering following them. Iskall was still reeling from the kiss as he stumbled down the hall with Cub, and he suddenly found himself in a dimly lit bedroom. He twisted out of Cub’s grip, though the motion made him dizzy and unbalanced, and he glared at the other hermit, who wasn’t smirking, just watching Iskall struggle to stay on his feet.

“Hey man, if you don’t want to do this, we don’t have to.” Cub said, but his calm words just pissed Iskall off more.

“No way man! I’m going to dom the hell out of you!” He lurched forward and managed to sort of pin Cub to the wall, one hand going behind Cub’s head and pressing their lips together once again. The older hermit just chuckled into the kiss, sliding his arms around Iskall’s waist and pulling him closer, their bodies slotting together as their tongues battled for dominance. Unfortunately for Iskall, it was a rather one-sided battle that Cub easily won, though that didn’t stop Iskall from continuing to fight. Iskall felt Cub’s arms tighten around him, then suddenly he was being spun around and he felt his back pressed up against the cool, solid wood of the wall. Vertigo hit hard at the sudden spin, and Iskall groaned lightly, actually glad to have the wall behind him as support. Once the room stopped spinning, he growled into the kiss and used his hand to tilt Cub’s head, giving him a better angle and changing the kiss. As he did so, he slid his other hand up, under Cub’s shirt, a little surprised at the toned, well-defined muscles he found there. He had been expecting at least a little bit of pudge, but no, Cub was fit as hell and Iskall found himself exploring the planes of muscle he’d found as his cock grew stiff under the dress. They broke the kiss and Iskall found he was panting, and out of breath, his knees feeling weak, though he blamed that on the alcohol running rampant in his system and not Cub or his delicious mouth. Nope, definitely not that.

The brunette had to hold back a small moan when he felt Cub’s mouth start to explore his neck, the soft lips and light sucking setting his nerves alight and making him shiver. He felt the other’s mouth move along his neck, sucking at various points and even biting lightly, when the older man reached the junction between his neck and his shoulder, Iskall squirmed and bit his lip to stop a wanton moan from escaping. Holy shit that felt good. Unfortunately, Cub seemed to have noticed his reaction and kept teasing that spot, sucking hard and making Iskall’s back arch away from the wall as he bit his lip, almost hard enough to draw blood. He’d never felt this kind of pleasure before, it made his knees weak and it was like every nerve in his neck was extra sensitive, with even the slightest touch sending sparks of pleasure down his spine.

To distract Cub from continuing to abuse his sensitive neck, Iskall pushed the other’s shirt up, trying to get him to take it off. Cub chuckled and pulled away, leaving Iskall leaning heavily against the wall, grateful to finally get a chance to catch his breath. The older hermit slid his lab coat off his shoulders, letting it pool on the floor, then pulled his shirt off, dropping it to the same pile and revealing his torso. Iskall stared at the expanse of pale skin that was now bare, trying not to admire the strength and definition of the other’s muscles, but goddamn. Cub noticed his staring, and a smug smirk curled his lips once again, making Iskall scowl. But Cub didn’t stay there too long, the aching in his pants compelling him back to Iskall, and back into their kiss. Cub brought his hands up and pulled the straps of the dress off Iskall’s shoulders, letting the top part fall, then worked on the back of the blouse, expertly undoing the buttons until the shirt was loose enough. He pulled away from the kiss, and immediately pulled the shirt up, and off, tossing it to the floor and leaning back a bit to admire Iskall’s now bare torso. Iskall couldn’t help but feel embarrassed as Cub looked him over, he wasn’t quite as toned as Cub was, he had a bit of pudge around his stomach, and he was still wearing the dress and pigtails, which only added to his embarrassment. But Cub didn’t mock him, like Iskall thought he would, the man just looked Iskall over, a hungry look in his eyes, before leaning in and whispering a growl into the brunette’s ear.

“You look beautiful, Princess, and I can’t wait to hear you scream for me.” Iskall flushed at the compliment and rather than it making him angry, it actually turned him on. What the hell was wrong with him?? Why was this hot!? He let out a small groan, and Cub attacked the other side of Iskall’s neck, the one he hadn’t already left multiple hickies on, and started to suck and bite, once again leaving Iskall feeling weak and more turned on than he’d been in a very long time. Soon Cub’s mouth moved down, leaving a trail of kisses and hickies in a meandering path that eventually found its way to Iskall’s nipple, which he playfully flicked with his tongue. Iskall gasped, the feeling was pleasant and almost ticklish, and when Cub sucked lightly on the bud, Iskall let out a small giggle, squirming against the wall. Cub pulled back with a smirk.

“Ticklish there, Princess?” He asked, and Iskall blushed at the nickname, feeling a strange surge of arousal, he refused to make eye contact, keeping his gaze to the side of Cub, rather than on him. The older hermit just chuckled and wrapped his arms around Iskall’s waist, lifting the brunette off the ground and making him yelp and cling to Cub.

“Woah! Cub, what’re you doing!?” Iskall tensed, he hadn’t been carried like this since he was a child, and it drove home just how strong Cub really was, making him shiver a bit. Cub just laughed and carried Iskall over to the bed, dropping him on his back and crawling over him. Iskall was about to complain, but the comment died on his lips when he looked up at the image of Cub looming over him, his eyes burning with an intense hunger and lust that Iskall had never seen before. He felt like his face was on fire from how much he was blushing, but he found he actually enjoyed the attention, and felt the urge to kiss the other hermit. He resisted for a moment, then gave in and reached up, pulling Cub into a lip-bruising kiss.

He gasped when he felt Cub’s hands on his thighs, bare fingers sliding up and over his boxers to tug at the waistband, almost like he was asking. Iskall broke the kiss and lay there panting for a moment while Cub gave him a questioning look. Was he seriously asking permission!? Iskall felt his face heat up even more and looked away, groaning and giving a quick nod. That was all Cub needed, Iskall felt his boxers pulled down, lifting his hips a little to help them slide, and finally they were gone freeing his throbbing erection. He was left in nothing but a pale blue checkered dress, that was falling off of his torso, while the skirt was riding up, showing most of his thighs and a serious tent that had formed in the middle. It was more embarrassing than just being naked, so he started to wiggle out of it, pushing the skirt down his hips. He barely got it down an inch, when Cub grabbed his wrists and yanked them above his head, Iskall letting out a frustrated growl.

“Hey-!”

“Ah, ah, ah, Princess, that needs to stay on.” Cub chided, smirking down at Iskall, who glared back.

“You are such an asshole.”

“I know~” Cub chuckled a bit as he released Iskall’s wrists and the brunette sulked, but didn’t try to remove the dress again. Cub lifted the skirt just enough so he could see Iskall’s cock and smirked, licking his lips before diving in, dragging his tongue up the side of the shaft and making Iskall moan softly. The brunette gasped quietly and let his head fall back, closing his eyes and just enjoying the feeling. This was something he was much more familiar with, and it was easy to relax into the feeling of warm lips and tongue pleasuring his cock. He was so into the feeling, that he barely noticed an odd click from Cub’s direction, and he nearly jumped out of his skin when he felt something cool and wet brush past his taint and touch his ass. He snapped his head up to look at Cub, who still had his mouth wrapped around Iskall’s dick, but slowly pulled off.

“Only if you want to.” Cub said quietly, and Iskall felt his confidence from earlier waver, he honestly hadn’t thought that he would be the one bottoming, but here he was. He bit his lip as he thought about it, everything so far had felt good, and well, obviously being on the recieving end of anal couldn’t be too bad, he’d fucked pleanty of people who all loved it. He realized he was talking a while to answer and glanced up at Cub, who was just calmly watching him, waiting for an answer but not pushing one way or the other. Iskall never would have thought that Cubfan would be the one to take his ass for the first time, but, well, the guy was insufferable, but he’d been nothing but a gentleman since they started. Iskall sighed and flopped back onto the pillow.

“Fuck, just, go ahead.” He groaned, not daring to look at the older hermit as he spoke. He heard Cub chuckle lightly.

“Don’t worry, I’ll go easy on you.” Iskall felt Cub’s clean hand slide under one thigh and lift it, setting it so it was bent, but still comfortable, and Iskall moved his other leg into the same position, earning a pleased rumble from Cub. Why did that noise make his cock twitch?

Iskall stiffened a bit when he felt the cool wetness touch his hole again, but he didn’t jump, just took a deep breath and tried to relax as Cub slowly pushed a single finger in. It burned a little bit, but not as bad as he’d thought it would, and as Cub started to move it back and forth slowly, the friction did feel nice. Iskall felt himself actually relaxing, the lack of pain and small bit of pleasure definitely helping with that. Apparently Cub felt him relax too, because it only took a moment before a second finger started to join the first. This one was a bit more uncomfortable, but still not bad, just a bit of burn, like the feeling you get during a workout when you really work your muscles hard. He let out a small moan as the fingers started to slowly fuck him, sliding in and out easily with how much lube Cub was using. He kept it to just those two for a while, which Iskall didn’t mind, especially when Cub’s mouth once again wrapped around his cock, and he let out a low moan.

After a bit, Iskall found himself rolling his hips in time with the fingers pistoning in and out of him, while Cub’s mouth moved in time as well. It actually felt really damn good. Too bad that didn’t last when the third finger started to push in. Iskall hissed slightly at the burn of the third finger, he stayed mostly relaxed, but it only helped so much, his ass was being stretched in a way it never had before, and it was resisting a bit. But Cub took it slow and kept his mouth moving, the pleasure slowly mixing with the burning and making the stretch feel pretty damn good. Iskall let out a moan and rolled his hips again, encouraging Cub to start slowly thrusting his fingers as Iskall melted under him. It was like nothing he’d ever felt before and it was incredible.

Just as he was starting to get back into the rhythm, Cub pulled away, his fingers leaving Iskall’s hole and causing the brunette to let out a groan that sounded suspiciously like a whine. Iskall could hear the rustling of fabric and looked up, but immediately wished he hadn’t. Cub had undone his pants and freed his cock, and it was a lot bigger than he’d expected. Iskall actually felt himself gulp at the size of the older hermit’s package, the idea of taking it in his ass making him more than a little nervous. He glanced up at Cub and saw the other watching him with a soft look, so he quickly looked away, his face flushing.

“Hey, Iskall. I’m not going any further unless you ok it. I don’t want to do anything you’re not cool with.” Cub’s voice was deep with arousal, but soft and Iskall let out a groan, he wasn’t exactly sure about this, but sat up and pulled Cub into a kiss, making the older hermit let out a small, startled noise. Iskall broke away just enough, their lips still brushed each other, but he could speak.

“Just fucking do it, before I get fed up and flip you over.” He growled, making Cub chuckle.

“As you wish, Princess.” Iskall flushed brighter at that, and lay back down on the pillows, watching as Cub stripped off his pants, then lifted Iskall’s thighs as he got into position. Iskall just focused on breathing, taking deep, slow breaths, though his breathing hitched when he felt the head of Cub’s dick touch his slick entrance. Then, he was slowly pushing in and Iskall let out a whimper, feeling his walls stretch and struggle to accommodate Cub’s girth, the burning actually making him gasp for air. Iskall balled the sheets in his fists and screwed his eyes shut as he tried desperately to relax his muscles, the burning slowly morphing into an almost overstimulated sort of pleasure. He finally felt Cub bottom out, and let out a breathy whine.

“Wait, wait, please wait.” He practically begged, feeling almost overwhelmed by all the sensations going off in his body. Cub leaned down and wrapped both arms around Iskall, pulling him close in an oddly intimate gesture.

“Don’t worry, I’m not moving ‘till you tell me to.” Cub rumbled as Iskall fought to catch his breath. They lay there like that for what seemed like ages as Iskall slowly adjusted, the stretching feeling both mildly painful and incredibly pleasurable. Iskall found himself releasing his death grip on the sheets, and wrapping his arms around Cub’s neck. Finally, he felt ready and let out a sigh.

“O-okay. Go slow.” Cub nodded and almost agonizingly slowly pulled out, just a few inches, then pushed back in, just as slowly. Iskall let out a small moan at the feeling, the friction felt good, and was definitely helping in pushing everything more towards pleasure than pain. He felt Cub pull out again, this time a little further, then back in. Out a little more, then all the way back in. It definitely felt good. Iskall let loose moans as the other moved, his thrusts also slightly speeding up as he went. He was still thrusting slowly, but by the time he was pulling all the way out, it actually felt like he was thrusting, rather than just dragging his cock along Iskall’s insides.

Iskall squirmed impatiently under Cub, and the older got the message, speeding up his thrusts a bit more, which earned him even more moans from the brunette, his visible eye closing as he felt himself getting lost in the pleasure. Cub’s thrusts continued to increase in speed until he found a good rhythm, that had Iskall practically writhing. It felt incredible! Iskall was mentally kicking himself for not trying this sooner, it felt so completely different from topping, but in a good way. A way that made his legs feel like jelly. He wasn’t going to stop topping after this, because he still loved it, but he was definitely going to try bottoming a bit more. He tried his best to roll his hips to meet Cub’s thrusts, it took a while, but eventually he got it, the sound of skin slapping against skin filling the room as their hips met. Cub groaned in pleasure and leaned in toward Iskall’s ear.

“Call me Daddy.” He growled, and Iskall’s eye snapped open in surprise.

“S-seriously?!” Cub tightened his grip on the brunette’s waist and gave a rough thrust, growling and causing Iskall to give a cry of pleasure. “Fuck! Ok!” He swallowed hard, then spoke in a breathy tone, almost whispering. “D-daddy…”

“Louder.” Cub commanded, giving another rough thrust, this one directly hitting Iskall’s prostate.

“Daddy!” Iskall almost screamed the word, his back arching off the bed as he clawed at Cub’s back.

“Good boy.” Cub’s thrusts got rougher, and he aimed for that spot, brushing it or directly hitting it every few thrusts. Iskall felt like he was losing his mind, each time Cub brushed by his prostate, it would send sparks through his system, like electricity lighting his every nerve. He felt dangerously close to coming, and could feel his cock bouncing against his stomach, achingly hard and neglected.

“Daddy, please!” He moaned, it was embarrassing as fuck to be calling Cub daddy, but he sure as hell wasn’t going to stop. “I wanna cum!” He begged, his voice breathy and desperate. Almost immediately, one of Cub’s hands was wrapped around Iskall’s cock and stroking it in time with his thrusts, Iskall desperately scratching at Cub’s back as pleasure overwhelmed him.

It only took a few moments, then Iskall was cuming with a moan of ‘daddy’ rolling off his tongue as every muscle in his body tensed, his arms locking around Cub and his ass clenching down hard, then fluttering as Iskall started to twitch. Spurt after spurt of cum splattered between their bodies, coating both of their stomachs in the sticky, white substance. Cub slowly came to a stop in his thrusts, feeling Iskall spasming around him and watching the brunette’s body twitch with the aftershocks. Iskall felt completely drained and let his arms fall from around Cub’s neck, just laying there, panting, for a few moments. The older hermit leaned down and pressed their lips together in the gentlest kiss of the night, Iskall returning the kiss in his blissed-out state. Cub let him lay there for a bit before he spoke.

“You think you’re alright to continue?” He asked. Iskall groaned lightly.

“I-I don’t think so… but we can try.” His voice was raw from all the moaning. Cub nodded and started to slowly pull out, but Iskall flinched and hissed in pain.

“That sounds like a no.” Cub chuckled a bit and Iskall let out a breath.

“Yeah, definitely. Sorry man…” Cub pulled the rest of the way out as slowly and gently as he could, though Iskall still grimaced.

“Nothing to be sorry about. You were incredible, Princess.” Cub gave Iskall a quick peck on the lips, and despite everything they’d just done, it still made Iskall blush.

“Y-you were too… Daddy.” Cub gave a pleased rumble at that and flopped onto his side next to Iskall. The brunette glanced down at the still obviously rock-hard dick Cub was sporting. “Uh, did you want help with that..?” He asked.

“Nah, it’s fine. Maybe tomorrow morning, if you’re feeling up to it.” Cub chuckled and Iskall followed suit, turning to face Cub and curl up against the older man’s chest.

“We should clean up…” He mumbled, already feeling sleep calling to him, probably due to the large amount of alcohol still in his system, plus the recent orgasm.

“Tomorrow…” Cub sighed, pulling a blanket out of his inventory and throwing it over them, since the blankets on the bed were currently trapped under them.

Iskall realized he was still wearing the Dorothy dress and shoes, but he didn’t care enough to take the dress off, so he just wiggled and kicked the shoes off, hearing them land somewhere in the room. Cub gave a chuckle at that, then pulled Iskall close, the two quickly dropping into sleep, cuddled up together.

-

The next morning, Iskall woke with a splitting headache, it was so bad it almost totally masked the pain in his ass, until he moved. He groaned as he shifted, his head pounding and his ass sore, he also had dried cum caked to his stomach, which was now cracking and pulling at the hairs there.

“Ow…” He groaned, hearing a sleepy chuckle from next to him. He rolled his eyes internally, since if he tried to actually do it, he’d probably puke from the pain, and buried his face in Cub’s chest, hearing another, more awake chuckle from the other man.

“So, which hurts worse right now, your ass, or your head?”

“Head…” Iskall whined, his head throbbing in time with his heart. Cub chuckled a bit, then Iskall felt him shift away from him, making the brunette whine in protest.

“Don’t worry, I’m just grabbing you some water and healing potion from the side table.” Iskall looked up at that, and luckily the curtains were drawn and the room was nice and dark, so it didn’t make his hangover any worse. He gladly accepted the healing potion, downing it, and feeling it surge through his body, easing most of the pain, with a sigh, he then took the water and downed it too. He felt a million times better, though he definitely still ached, it wasn’t nearly as bad.

“Thanks.” He glanced over at Cub and felt his face heat up, not only had he gotten fucked for the first time last night, but he’d made a damned fool of himself, getting all worked up and acting like a bit of an asshole. He sighed. “Sorry about being a jerk last night… And, uh, thank you…”

“You’re forgiven, and what for?”

“For… being so nice? I guess? For making my first time kinda incredible…” He couldn’t look Cub in the eye as he spoke, it was probably the weirdest conversation he’d ever had, but he wanted Cub to know he was grateful. There was a pause, then Cub spoke.

“Well shit…” Cub chuckled and Iskall glanced up, seeing a rather awkward, almost guilty look on the other’s face.

“What?”

“I, uh, didn’t realize that was your first… Now I feel like a bit of an ass.” Iskall let out a small laugh at that.

“For what? You were a total gentleman last night, despite me being a jerk at every turn.” They both chuckled and relaxed.

“Well, I guess, I’m glad you enjoyed yourself. I probably would have done things differently if I had known, but, yeah, glad you enjoyed it anyway.”

“Yeah…” Suddenly a thought occurred to Iskall and he groaned. “Oh no, please don’t tell the other hermits. I’ll never live this down.” Cub laughed lightly and gently rubbed Iskall’s back.

“Don’t worry Princess, my lips are sealed.”

-

Unfortunately for Iskall they didn’t really need to tell anyone. When they came out for breakfast, it was pretty obvious to everyone what had happened, given that Iskall was limping slightly and Cub looked just the slightest bit smug. But no one gave him shit for it, they were mostly just impressed that the two had actually had sex rather than killing each other.

**Author's Note:**

> I’ve created a tumblr blog - https://aaronampora-ao3.tumblr.com/  
> Feel free to drop any requests you may have, ask questions, and/or follow for updates and random musings while I write.


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